So as I stated I would, I did business with this dude again. Things did not go quite as smoothly this time as they had previously.
I sold him my electric autumn, which he paid quickly for, and was awesome throughout the initial transaction. When it arrived at his house, he texted me saying he was unhappy with the fit of the garment, and that he wanted to figure out if there was some way he could return/exchange it, to which I happily abided. We figured that we would make an exchange; I would send him some different items, and he would send me back the Electric Autumn. I fulfilled my side of the deal, and didn't get anything, or hear from him for weeks.
When KushLover did hit me back, he was very apologetic about everything, explained that he was in a tough financial situation, and that he would stay in contact better, and we would work things out. I figured there was no risk in going with it, I wouldn't lose anything else. Very recently, he did follow up, and offered to pay me a very reasonable price for the sweatshirt that he never sent, and he would just hold onto it.
Overall, I would do this exact transaction again, and should KushLover ever want to buy anything from me again, I plan to do business with him. There was a sever communication breakdown, but in the end, both of us got what we wanted, and he made a legit move, and did the right thing.
I'd say buy from/sell to this guy, I don't see this situation happening again.